Welcome to Management: Please Proceed With Delusions of Control
What the management gurus won’t tell you [Not Obvious: Part 4]
The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us:
Part 1: Why Work Advice Fails Us (intro)
Part 2: Burnout, Balance, and the Bullshit in Between (on “hard work”)
Part 3: You Will Never Feel Done (on “productivity”)
Ahhh, management… the noble science of keeping everyone happy, productive, and aligned while pretending you have control over what happens next.
The workers look up, longing for a shepherd to guide them to prosperity. Or at the very least, steer away from misery. The bosses look down, longing for a proxy (paid far less), to implement their undoubtedly clear vision.
In the fantasy-land of “good management,” we are loved by all:
To our team… we’re the wise, effortless leader. Hands-off but always in tune, like the cool mom/dad on the team. We inspire, delegate flawlessly, and offer up insight when needed. And they’ll certainly never wonder if they could do our job better!
To our bosses… we are the golden child – exceeding goals, sidestepping political landmines, never passing stress back upward. In fact, did you hear? They’re reserving a spot for us up the ladder next year, a cell higher up and with a better view. And they’ll definitely never wonder if someone else could do our job better!
Guiding us through this impossible balancing act? The Management Messiahs, armed with their 1:1s, OKRs, and 10 ways to 10x our team (personally, I’m more of an 11x guy). My bookshelf groans under the weight of leadership advice, ranging from retired generals → turned-out-to-be-a-fraud CEOs → that guy who runs a lot.
And the self-help industrial complex (after successfully making us healthier and happier), double downs on dishing out wisdom, serving up platitudes from influencer-types whose most challenging direct report is a social media algorithm.
But anyone who has actually managed knows: this land is full of myths that sound great in theory but get messy in real life. That adherence to certain prescribed strategies won’t inevitably lead to success. That the notion of a 'good manager' is a well-crafted illusion, promising certainty in a role built on uncertainty.
I’ve seen too many contradictions to believe that management is a science. So, let’s talk about the myths. The ones that fill bookshelves, fuel leadership offsites, and haunt every manager who wants to get it right.
Bad Managers
Let’s get the obvious out of the way: there are a lot of “bad managers” out there. Even after we skip over the most egregious acts of immorality (e.g. harassment, fraud, general evil), it’s not too hard to spot the asshole in the office.
We all know at least one manager who makes everyone miserable. Me? One summer in college, while roofing, I had a boss who spewed so many racist and sexist slurs that the memory of him has stuck longer with me than the tar that got on my clothes.
But beyond the obvious, I’m skeptical of our definition of a “bad manager.”
One guy I worked with was disliked by many (think drill sergeant), but in chaos, he was necessary. Another time, I inherited a team that was nearly 100% not good; either deceptive under-achievers or folks who didn’t fit the future of the company. If you asked them, I’m sure I would have failed their “good manager” test. Hell, maybe I did – most were gone within the year.
Even the best business-builders of our time seem pretty horrific to work for. Scratch beyond the surface of any of your idols…
"Steve was so hard on people—relentlessly critical, often cruel. People would regularly break down in tears." – early Apple engineer
Of course, no experienced manager wants you tracking down their ex-employees to dig up dirt. It wouldn’t be that hard to find my flaws, that’s for sure. You might even get some eager volunteers.
But spotting a “bad manager” is harder than it seems. One “right” decision over here will definitely piss someone off over there. What you call an “asshole” might to me be an “asset.” Please don’t overthink that sentence.
So what about spotting the so-called “good managers”?
Good Managers
Let’s work through some of the conventional wisdom:
“Don’t micromanage.”
Okay, here’s some universal advice, right? Everyone hates micromanagers.
Except sometimes you need to micromanage. Wait, what?!?
The new employee. Or the one with performance issues. The key project or product release. The key customer. The company crisis. The critical process that cannot fail.
The defining moment of my career was when I led the launch of our business’ pivot to a new model. So you better believe I micromanaged the hell out of that project.
Sometimes you need to get up in people’s business and demand excellence. Unless, of course, that backfires and makes everything worse.
“Be a Servant Leader.”
Everyone loves a Servant Leader, especially the people getting served.
It works great…when the team is already high-functioning, clear on goals, and full of competent/collaborative people. It's management on easy-mode. Anyone can serve a team that runs itself.
But if your team needs direction or correction, what they actually need is a goddamn leader! When the company is collapsing, people are lost (or disagree), when the strategy changes overnight – you don’t want a Servant Leader attempting to create buy-in across every person and need. You need someone to dictate, not facilitate.
“Lead with transparency.”
…Right up until the moment where your team spirals into violent panic.
People say they want truth. What they really want is comfort.
Tell them all, openly, about your doubts as a leader, the fragility of your command, that their work is meaningless, their jobs are threatened by the tides of AI, that their (and your) loyalty is conditional… and watch as they crumble.
Transparency is a virtue. But so is knowing when to shut up.
“Be accountable.”
No one likes an unaccountable leader. For example, you need to “accept feedback like it’s a gift.” But if you think all feedback is useful, you’ve never been ambushed by a few detractors hijacking a meeting while everyone else tries to move forward.
Being accountable also means taking the blame when something goes wrong. You shield the team from the shit. Employees love autonomy, except when they autonomously make a huge mistake.
But be careful: take too much blame, and people might start wondering if you really are to blame! The trick is to own the failure in a noble-sort-of-way, where everyone knows you’re not really at fault. Simple, right?
“Delegate work to your team.”
Delegation is essential. But delegate too much and they’ll get overwhelmed. Worse, they’ll start wondering: “wait… what do you even do here?” Never a good question.
You should also “trust but verify.” Which means that you trust your employees, but monitor them closely in case they aren't trustworthy. And they’ll always make the right decisions because they know what you want, because you know what you want!
So encourage mistakes. Let them take risks. Just… not too many risks. Not too many mistakes! Otherwise, they need to go.
Where’s that line? Good luck finding it!
“Only hire A-players.”
The first person I ever managed was a guy named Will Wiet; still one of the best I’ve worked with (to all my former teammates reading this: you too, were one of the best!). But Will being great probably had more to do with him than me. Which raises the question: was I a good manager or did I just manage a good employee?
Not everyone will be an A-player (if you can even define that). Some of you will say: “everyone needs to be great!” Well, I don’t think you’re grounded in reality.
Sometimes A-players become A-players over time. Sometimes they aren’t “A” here, but would be an “A” over there (or without you as their manager). I worked with someone who I thought was a “B” player, but turned out to be an “A” player in another role. Or they’re an “A” this quarter, but a “B” the next (a fireable offense!). Sometimes you can’t pay enough for an A-player.
And let’s be honest: if they were that good, what are they doing working for you?
“Set clear goals. Manage what you measure.”
You need the team to work on the most important thing. Which is obvious to begin with, right? But don’t drop the other important things. Like when a client threatens to leave. Or new information upends your strategy.
We set goals. Measure progress. Implement OKRs. In our desperate search for order, we pretend human activity can be turned into pixels on a spreadsheet.
I’ve used all these before and they DO work… until they’re gamed, misinterpreted, and weaponized against common sense. Here’s how it plays out:
Pick a metric.
Incentivize it.
People chase the metric (because incentives).
Build process to keep hitting the metric.
Automate parts of the process.
…and before long, the metric becomes one with the company, embedded inside a bureaucratic nightmare that only exists to sustain itself.
KPIs don’t always measure excellence. They measure compliance. And they can be a crutch for the shallow-minded who would rather count than comprehend reality. Some of the most important things aren’t measurable: culture, customer relationships, burnout. Ignore the vibes at your own risk.
But, but, but – "you don't manage what you don't measure!" Yeah. That's the problem.
So… what makes a good manager? Depends on what you need.
Beyond Good & Bad Management
Let me be clear: I'm not saying abandon all management advice. Just that it isn’t as obvious as they make it seem. While the maxims can contain elements of truth, their blind application can create unintended consequences. They're tools, not truths.
Leadership is basically the art of making decisions while always wondering if you're doing it wrong. It invites doubt – from those you manage, those who manage you, and your own 3AM conscience. And work isn’t a predictable, rational environment where logic prevails. No one has perfect control and neither will you. Once you accept this, you stop looking for the right answer and start figuring out what works now.
When I think of the good managers I've had, the one constant is they were the right manager for me at that time, but would’ve been wrong at another time.
If "good managers" exist at all, they're those who embrace the ambiguity. Adaptable people with diverse tools for diverse problems. They don’t see choices as good vs. bad, but trade-offs with unpredictable consequences. They can live with the endless loop of contradictions, while discarding the warped expectations created by management mythology.
If you’re going to lead, then lead. But do not be fooled into believing there is some universal path to doing it “right.”
And if you somehow do it all well? Then, what are you doing here? Go forth! You’re the management guru now (just hope no one asks too many questions).
Bonus: Ambiguous Advice
▸ “Start with why.”
It’s a fancy way of saying: “because I said so.”
▸ “Lead by example.”
Wait! No, not that example!!!
▸ “Hire slow. Fire fast.”
Try no to get sued.
▸ "People don’t leave bad jobs; they leave bad managers.”
I’m also able to offer you a combo pack!
▸ “We’re like a family here.”
Dysfunctional, passive-aggressive, and full of unresolved trauma.
Next up, I explore the advice around “follow your passion:”
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This makes me think of a quote from Jason Fried's book, "It Doesn't Have to Be Crazy at Work," that has always resonated with me.
“There are many reasons to be skeptical of best practices, but one of the most common is when you see someone deriving them purely from outside observation about how another company does it…Furthermore, many best practices are purely folklore. No one knows where they came from, why they started, and why they continue to be followed. But because of that powerful label — best practice — people often forget to even question them.”